Imidazole → 8-(Tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde

HRID 876401

反応式

HRID 876401 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[O:13])[CH:8]=[CH:7]2.N1C=CN=C1.[C:19]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl>[Si:23]([O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[O:13])[CH:8]=[CH:7]2)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:25])[CH3:24]

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5993428-Hydroxy-2-quinolinecarboxaldehyde

生成物 1

HCID 585670828-(Tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde収率 83%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

8-Hydroxyquinoline-2-carbaldehyde (5.00 g, 28.9 mmol) and imidazole (4.32 g, 63.5 mmol) were dissolved in DCM (50 mL) under N2. The reaction mixture was cooled to 0° C., followed by addition of tert-butylchlorodimethylsilane (4.94 g, 31.8 mmol). After stirring for 16 hours at ambient temperature the reaction mixture was partitioned between DCM and H2O. The organic layer was washed with H2O and aqueous saturated NaHCO3, dried over Na2SO4, filtered and concentrated under reduced pressure to afford an orange oil. The residue was purified by flash column chromatography (10:1 Hexanes/EtOAc) to provide 6.85 g (83%) of desired product as a yellow/orange oil.

後処理

  1. customwas partitioned between DCM and H2O
  2. washThe organic layer was washed with H2O and aqueous saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford an orange oil
  7. customThe residue was purified by flash column chromatography (10:1 Hexanes/EtOAc)

出典と根拠

ORDレコード
ord-a4b6dd338c934e2d88337b6f40bda95d
出典データセット
uspto-grants-2015_03
特許番号
US08987251B2

関連ノート

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